This application claims the benefit of the filing of U.S. Provisional Application Ser. No. 60/001410 filed Jul. 25, 1995.
The present invention relates generally to novel herbicidal compounds and methods for their use in controlling unwanted plant species in agriculture. In particular, the present invention relates to novel optionally substituted phenylmethoxyphenyl or phenylmethylthiophenyl heterocycles and their use as herbicides.
U.S. Pat. No. 5,032,165 (Miura et al.) discloses herbicidal (3-substituted phenyl)pyrazole derivatives of formula: ##STR3## wherein: X is halogen;
R.sup.1 is lower alkyl or lower haloalkyl; PA1 R.sup.2 is --A--R.sup.5 wherein R.sup.5 is H, lower alkyl or lower haloalkyl, and A is O or S; PA1 R.sup.3 is H or halogen; and PA1 R.sup.4 is formyl, nitro, --CO--B--R.sup.6 wherein B is O, S or --NR.sup.7 and R.sup.6 and R.sup.7 are the same or different and each denote H, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxycarbonylalkyl, cycloalkyl, lower alkylsulfonyl, lower alkoxyalkyl, or di(lower alkoxy)phosphinylalkyl, and when B is O, R.sup.6 can be an alkali metal atom or a quaternary ammonium salt!, --DR.sup.8 wherein D denotes O, --S(O).sub.n (n being an integer of 0 to 2), or --NR.sup.9 --, and R.sup.8 and R.sup.9 are the same or different and each denote H, alkyl, haloalkyl, lower alkenyl, lower haloalkenyl, lower alkynyl, lower cyanoalkyl, lower cycloalkyl, lower alkoxyalkyl, lower alkylthioalkyl, lower alkoxyalkoxyalkyl, lower alkylsulfonyl, di(lower alkyl)aminosulfonyl, aminosulfonyl having one or more substituents which are the same or different and selected from H, lower alkynyl and lower alkyl, phenylalkyl or phenoxyalkyl optionally having on the phenyl ring, one or more substituents which are the same or different and selected from halogen, lower alkyl, lower haloalkyl and lower haloalkoxy, tri(lower alkyl)silylalkyl, or di(lower alkoxy)phosphinylalkyl!; or --(CHR.sup.10).sub.m --CO--E--R.sup.12 wherein E denotes O, S or --NR.sup.11 wherein R.sup.11 is as defined below; R.sup.10 denotes H or lower alkyl; and R.sup.11 and R.sup.12 are the same or different and each denote H, alkyl, haloalkyl, lower alkenyl, lower haloalkenyl, lower alkynyl, lower haloalkynyl, lower alkoxyalkyl, cycloalkyl, lower cyanoalkyl, lower alkylthioalkyl, alkoxyalkoxyalkoxy, tri(lower alkyl)silylalkyl, di(lower alkoxy)phosphinylalkyl, phenyl optionally having on the phenyl ring, one or more substituents selected from halogen, lower alkyl, lower haloalkyl and lower alkoxy, or phenylalkyl optionally having on the phenyl ring, one or more substituents selected form halogen, lower alkyl, lower haloalkyl and lower alkoxy; or R.sup.11 jointly with R.sup.12 forms piperidino or morpholino, and when E is O, R.sup.12 can be an alkali metal atom or a quaternary ammonium salt; and m is an integer of 0 to 3!. PA1 Q is a heterocycle selected from: 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, 3,4,5,6-tetrahydrophthalimid-1-yl, 1-(1-methylethyl)imidazolidin-2,4-dion-3-yl, 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-on-1-yl, 4-chloro-4,5,6,7-tetrahydroindazol-2-yl, 4-methyl-1,2,4-triazine-3,5-dion-2-yl, 8-thia-1,6-diazabicyclo4. 3.0!nonane-7-on-9-ylimino, or 1-methyl-6-trifluoromethyl-2,4-pyrimidinedione-3-yl; PA1 W is O or S; PA1 X is H, F, or Cl; and Y is H, or X and Y taken together may be --OC(CH.sub.3).sub.2 CH.sub.2 -- to form a 7-substituted-4-benzofuranyl moiety; PA1 R' is H or methyl; PA1 R" is --OR or amino, arylamino, alkylamino, alkenylamino, alkoxyamino, cyano or alkyl-, haloalkyl-, or arylsulfonylamino of the formula --N(lower alkyl)SO.sub.2 R.sup.9, or --NHSO.sub.2 R.sup.9 ; PA1 R is H, M, alkyl, cycloalkyl, lower alkenyl, lower alkynyl, or --CHR.sup.7 (CH.sub.2).sub.m O!.sub.n R.sup.8 ; PA1 Each of R.sup.1 through R.sup.6 are substituents on the heterocycle Q; PA1 R.sup.7 is H or lower alkyl; PA1 R.sup.7 is alkyl; PA1 R.sup.9 is alkyl, haloalkyl, or aryl; PA1 m is 0 to 2; PA1 M is a monovalent, salt-forming group; PA1 Z is H, F, Cl, Br, lower alkyl, phenyl, or methoxy and Z' is H, F, or Cl; or Z and Z' taken together may be --(CH.sub.2).sub.4 -- to form a tetrahydronaphthyl moiety; and the group --OA may be in the 2-, 3- or 4-position of the phenyl ring. PA1 R.sup.2 =lower alkyl, or lower haloalkyl; PA1 X=H, halogen, or lower alkyl; PA1 W=O or S; PA1 Z, Z.sup.1, Z.sup.2 are independently selected from H, halogen, straight or branched chain lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, cyano, lower cyanoalkyloxy,nitro, aryl, or aryloxy; or Z and Z' are adjacent to each other on the benzene ring, and taken together are --(CH.sub.2).sub.4 --; or Z.sup.2 is OA in the 2-, 3-, or 4- position of the phenyl ring; ##STR7## A is R.sup.3 is H, lower alkyl, halo, or; PA1 R.sup.4 =OH, straight or branched chain lower alkoxy, lower haloalkoxy, alkoxyalkoxy, alkoxyalkoxyalkoxy, alkoxycarbonylalkoxy, amino, lower alkylamino, lower alkoxyamino, lower alkylsulfonylamino, lower haloalkylsulfonylamino, lower (alkyl)(alkylsulfonyl)amino, or an agriculturally acceptable salt thereof; and PA1 R.sup.5 =halogen or lower alkyl ester. PA1 R is OH, straight or branched chain lower alkoxy, lower haloalkoxy, alkoxyalkoxy, alkoxyalkoxyalkoxy, alkoxycarbonylalkoxy, amino, lower alkylamino, lower dialkylamino, lower alkoxyamino, lower alkylsulfonylamino, lower haloalkylsulfonylamino, or lower (alkyl)(alkylsulfonyl)amino.
U.S. Pat. No. 5,262,390 (Theodoridis) discloses herbicidal 2-(4-heterocyclic phenoxymethyl)phenoxy!alkanoates of formula: ##STR4## wherein: A is a derivative of an alkanoate bonded to the phenoxy oxygen at the (.alpha.-carbon;